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A really dumb question - hats in the office?

I agree. My father and all of my uncles, plus my grandfathers all wore hats, daily. However, they would inevitably take them off when coming inside of someone's home or office. It was a sign of deep disrespect to wear a hat in someone's house and it would likely get knocked off of one's head if donned. We were taught from kids that we must remove our hats indoors and the military reinforced that. You could always tell what sort of family some of the young men came from by their manners.
 
Casual or not, there are some rules I go by
Inside, office, school, whatever.
Long pants (jeans with no holes in them, or regular pants) never shorts
Summer time, short sleave shirt or polo
Winter, long sleaves shirt
Shoes or sneakers (one colour, black or brown or white, other colours are for gym and pic nic)
And never ever wear any kind of hat or sunglases inside (only blind person can wear sunglases inside)
 
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